Time Will Tell
by RightSide
Summary: Gossip Girl meets Supernatural when Blair is kidnapped by a demon. With Dean by her side, she reenters the world she has come to know with a different set of ideals. Will she be able to return to her old ways? Will she want to?
1. Chapter 1

**Title: Time Will Tell**

**Author: RightSide**

**Rating: PG13/T… could be bumped to R for violence.**

**Pairing: Blair/Dean/Chuck/Nate**

**Disclaimer: I do not own Gossip Girl or Supernatural. Please do not sue me and my overly active imagination.**

**Summary: Gossip Girl meets Supernatural when Blair is kidnapped by a demon. With Dean by her side, she reenters the world she has come to know with a different set of ideals. Will she be able to return to her old ways? Will she want to?**

**A/N: For Supernatural, it is set before the pilot. Dean is around twenty. The Gossip Girl half is television based. It is set after episode 13, The Thin Line Between Chuck and Nate.**

**Chapter 1-**

Serena couldn't stop herself from opening her phone as the tone sounded, letting her know there was a new text message in her inbox. Still cuddled soundly against Dan's side, she flipped open her phone. It was from Gossip Girl. Squealing, she gained her boyfriend's attention and both read the message together.

"Sorry to be the bearer of bad news, Upper East Siders. She might not have been our favorite person, but Queen B wasn't found in her bed this morning. Is this latest piece of gossip an act, or is there a reason the police are searching high and low? Only time will tell. You know you love me. XOXO. Gossip Girl."

--

It was dark, so dark Blair couldn't make out a damn thing except for the black and the musty smell of cold, wet earth. A grunt sounded from behind her. Attempting to turn around and face the person, Blair found herself pinned down by something.

"Help," her voice cracked. Before she could blink, he was before her. While she was still blind, she could hear his heavy breathing. Then his hands were on hers, checking her binding and undoing it so fast she could hardly feel his movement.

"Blair Waldorf?" he asked gently. Confused, she backpedaled immediately. It was too fast, though, and she found herself falling back into the nothingness that surrounded her.

"Whoa there. I'm not gonna hurt you."

"Do you know how to get out of here?" she asked. Pushing herself up, she clung to him. Feeling his surprise, she tensed. Before she had the chance to let go, however, he clasped her hand and gave it a reassuring squeeze.

"Yes. Follow me." he began to pull her foreword, but she stopped him.

"That… it wasn't Chuck. I don't know what it was, but it could come back."

"Don't worry," he said, tone soothing, "It can't hurt you anymore." He set a quick pace. At first she could not understand why if the threat of that… that… _thing _was gone. But then she realized as she winced from the pain. He knew somehow, this man whose face she had not even seen in the light of day, that she had been cut several times over. The amount of blood she lost was having dangerous effects. Her legs buckled beneath her, body heavy and slowly growing limp as she became tired.

The last thing she remembered before she lost consciousness was his strong arms wrapped around her as he carried her out.

And then there was nothing but light.


	2. Chapter 2

**Title: Time Will Tell**

**Author: RightSide**

**Disclaimer and Summary: See Chapter 1**

**Chapter 2-**

He was handsome; she had not been expecting that. Somehow after their brief time in the cave together and the few moments when she woke up on the table of some man named Bobby, she had pictured him old, tall, bulky, and tattoo covered. In her mind's eye, his hair was long and white, maybe even a little scraggly and rough. What she found, however, was completely different.

When Blair's eyes opened and took in the world for the first time since she passed out, she had been aware of several things. One, she was not wearing the same clothes she had worn the night of her abduction. Two, she was covered head to toe with gauze. Three, she had no idea where she was.

Or when. Time had passed so strangely when she was out that she wondered just how many days had gone by. Lifting one of the makeshift bandages, she realized her long, deep wounds had been stitched perfectly. So well, in fact, that they would hardly leave a scar.

Searching her surroundings, she noticed that there were two single beds with a night stand between them. A television set on a dresser was on the wall opposite of her. The decorating was awful; everything was covered with pastel floral patterns and the smell of bleach. A sink was built into a counter in the back with two doors next to it, one of which marked with every type of lock known to man. From the looks of things, she was in a very, _very _cheap hotel.

"I told you, I had Bobby fix her up. She'll fine in no time. I'll just give her a ride home… I know she's rich… They'll be looking for some justice, but they won't dish it out on the guy who saved her… Yes, sir… I understand, sir… Bye." Blair recognized that voice. Curiosity striking, she laid back down at an angle that made her able to watch him with very little chance of him noticing her scrutinizing gaze.

The air caught in her throat when he finally came into view. He must have just showered and had been changing when he got his phone call. While he was wearing a pair of faded jeans, his incredibly toned chest was bare. Her mystery man was muscular, chiseled, and perfect in every sense of the word. Blair felt the urge to rake her nails across his abdominals, his various scars making her want him so much more. But she had to smile when she realized his face was just as handsome as the rest of him.

He was not clean shaven, but something told Blair that he liked it that way. His hair was dirty blond and spiked up naturally with beads of water still clinging to it. His eyes were honey. Even at such a distance they seemed to glisten. They flickered about the room, taking in everything, examining her so that she had to close her eyes for a moment to fake sleep. When she could no longer feel his gaze on her, she slowly resumed her assessment. He clenched his jaw, his cheek bones coming into sight, defined and gorgeous. Hell, his lips were even amazing.

With a smirk, Blair couldn't help but laugh. Her savior came in the form of a stunning man who couldn't have been any older than twenty. Sitting up, she decided to make her consciousness known. While watching him was entertaining, she wanted to know his name.

"You're awake." he said in a friendly tone, grabbing the white tee shirt he had set on the bed and haphazardly throwing it on. One of his hands reached down the front of his shirt, and he pulled out something to rest on the outside. It was a thin black chord with a golden pendant of some sort hanging from it. How she had missed it when she was ogling him, she wasn't sure. There was just so much to look at, she supposed, she could excuse missing one small necklace.

"How long have I been out?" she asked, making conversation.

"Three days. You had your lucid moments, but most of the time you were sleeping. I would have taken you to a hospital, but there hadn't been enough time and a doctor friend of mine lived near by. I had him stitch you up. You lost a lot of blood, but you should be fine." He sat on the bed next to her, gaze intent. There was something altogether fascinating about him. Even a person less talented would have been able to tell that he had seen more than his fair share of danger and heartache, yet he was able to smile and smirk and seem like a little boy unable to hold still.

Swinging her legs over the side of the bed, Blair saw what she was wearing for the first time. Large black sweat pants and an oversized blue tee. Both articles were clearly his. Raising an eyebrow, she gave him a questioning look.

"Your clothes were torn to shreds. I gave you some of mine."

"You undressed me?" he smirked at her obviously overdone look of horror.

"Is there anything you need to ask me. You went through hell back there. If there was anything you wanted cleared up or explained-"

"Who are you? And how do you know my name?" he looked slightly uncomfortable for a moment, but then he regained composure.

"My name is Dean Winchester. I hunt the monsters that live under your bed. I have since I was young enough to shoot a gun. When young girls your age were going missing I figured it was something down my alley. I came up from Virginia. I found out it took you. I hunted it down."

"So this is what you do? For a living? Do you get paid?" he smiled at her, a genuine smile that made her spine tingle.

"I tell you that monsters exist and you ask about the paycheck?" he laughed and shook his head, "I go around the country saving people, hunting things. It's the family business. I don't get paid, but I know enough credit card scams and hustling techniques to get me by."

"And you live like this? In cheap hotels? Alone?" Blair could not stop the pity from crossing her features as she said it. Dean nodded and explained more about how he had his father who was his general and sent him into battle when the occasion called for it. He had a brother who was in college, leading a normal life. His mother was dead.

"I'm going to need some help from you, though. See, this thing that attacked you, there could be more of them around here. If there are more, they'll come looking for you. I was able to track the one that took you because it just happened to be more clumsy than usual. If the others are good, they'll be able to snatch you out of your bed again without a moment of hesitation," at seeing the worry on her face, he continued hurriedly, "I won't let that happen, Blair. I'll protect you. I just need to be able to safeguard you without any of your relatives getting upset. You can probably guess that I'm not a fan of cops or questions. If you kill something that's wearing a person's face and tell them the thing you killed wasn't human, you'll end up in prison or in the psycho ward. I can't afford to get caught."

His golden eyes bore into hers, widening, asking for help. Blair had no intention of making things difficult for him. She would tell her parents that some man had taken her. She never saw his face. When she finally was able to break free, she screamed. Dean heard it, broke into the house, and found her. Then he accidentally killed the man responsible. Her parents wouldn't continue the investigation. They would leave the both of them be. Blair would say that Dean was a college student taking the semester off. She would complain that she only felt safe with him there because he had saved her. Her mother would be forced to let him stick around. Hell, Blair would even sneak him into her room to stay the night so he wouldn't have to watch over her from outside in the dark.

"Don't worry, Dean. It'll be fine. I know what to say to get them off your back _and _mine," she was going to end the conversation there and ask for a shower, but something in the back of her head was nagging at her, "The thing that attacked me, it looked like Chuck at first…" she let the statement fade off into a question.

"The Valais are probably the most disgusting creatures ever created. Honestly, they are some scary mothers. They have speed and agility on their side, but they also need to get close to their victims with as little struggle as possible. They pick your brain and take the form of someone you trust. A friend, a loved one. Then they make you come to them and make contact. After that, the rest is history. They take you to their lair, bleed you, eat you, toss the bones. Standard drill."

Shocked into numbness, Blair cleaned herself off and rummaged through Dean's clothing until she found a pair of pants that weren't beaten up too badly and a belt. Putting on the pair of three dollar flip flops Dean had bought her and another large shirt tied at the back so that at least some of her figure showed through, Blair was ready in no time and they headed out.

Opening the door, the light of day was bright and more beautiful than ever. In front of the room there were two vehicles. One was amazing. An old school Impala with a paint job to die for and completely restored interior. The other was a beat up Ford pickup truck with pealing paint and rust. Heading towards it, she got a shock as Dean stared at her dumbstruck.

"Hey, I might be a broke criminal, but a man has to have standards." he unlocked the passenger door of the Impala and Blair somehow managed to squeal and jump in. It had been too long since she had sat in the front seat of a car. Dean turned the ignition and the engine roared. Shoving a cassette- the very thought of one making Blair smile- into the stereo, AC/DC began to blare from the speakers.

Blair giggled. The beat of "Back In Black" was rolling over her in waves. Dean rolled down his window and she followed suit, enjoying the feel of the wind on her wet hair. No make up, no people to impress, no wondering if she was going to be humiliated by another manipulative counterpart. Banging her head to the music, she scrunched up her face and looked at Dean as she played air guitar. Grinning, he joined her, singing very loudly and off key. Oh, how she was starting to love that voice.

"Breakfast?" he asked. She nodded, but then thought better of it.

"I really should get home and let my mother know that I'm okay." Dean gave an understanding half smile.

"You really should eat, though. To keep up your strength. Here, we'll go through the drive-thru. What do you want?" he pulled a sharp right turn and swung quickly around the curve of the McDonald's parking lot. Blair became confused and then worried.

"I really don't want anything." she said softly, the image of her fat and oily playing in her head. She shuddered. Dean gave her a once over and laughed. It wasn't flirtatious or innocent, either. It was a mocking chuckle. He raised his eyebrows and gave her a strange look.

"You're like a stick. I am going to buy you a breakfast sandwich, and if you do not eat it I swear I will stop this car and not drive an inch further until you take a bite. Understood?" Any sign of a smirk was gone and his face became completely serious. Instead of an answer, she dropped her folded arms and sighed. Without a sound, she sat still as he ordered her a bacon something or other. She would throw it up later, in the privacy of her own bathroom.

"Here you go." he said after they got their food. She chewed in peace.

"You don't have the right to tell me what I can and cannot do." she burst, suddenly extremely upset.

"You are under my protection, and as long as I'm babysitting you I'm not going to watch you die from malnutrition."

"Wow. Big word. Surprised you didn't stutter over it. How long were you in school for? I'm betting you didn't last through junior year." Annoyed, Dean pulled over, turning the stereo off and letting the engine rest on idle.

"Yeah, and while I'm out saving lives you'll never be anything more than a pretty ornament on some asshole's arm. Sounds like a great future, princess."

"I'll have you know that I'm going to Yale. I am going to become an executive. My future looks pretty damn good. What in the hell are you going to do with yours?"

"I know exactly what my future is going to be. I am going to fight every single day of my life. I am going to scrape by on every cent I can, and I will save tons more ungrateful little rich girls in the process. And one day, not so far away, I am going to meet an evil son of a bitch that will get the best of me. I'm not expecting to make it past thirty. I have accepted that. But you know what? There will be hundreds of people alive because of my sacrifice. Can you say the same? When you marry Prince Charming and stay with him even though he has cheated on you multiple times, who will you be making that sacrifice for? Maybe it'll be for the kids. But mostly, everything you do will be for your own benefit."

There was silence for a long time. Blair stared out the window at the country side, the large city slowly coming closer, looming ahead. She wanted so badly to be his friend. Why, she didn't know. There was something about this boy, this man, that made her want to be someone other than Blair. But then her mouth caught a hold of her and made her follow until she was being as mean and insecure as ever.

An apology was needed, but she was going to have trouble voicing it. Especially when he was sitting there looking so guiltless. She was so wrapped up in her own thoughts, she was surprised when she heard him speak.

"I'm sorry." he said as if in a foreign language and he was unsure he had gotten its pronunciation correct.

"What?" she was in awe.

"I said 'I'm sorry'. I shouldn't have given you a speech. I'm just not in the best mood right now, and there has been a lot going on in my life lately. I shouldn't have taken it out on you. So, I'm sorry."

Blair smiled, "So am I. I really shouldn't have been so mean."

"Thank God," he said in a breathless voice, "I was getting so sick of not having the radio on." Right away he rummaged through his little box of cassettes and slipped another one in. Led Zeppelin started to play.

"Did you apologize just so you could play your music?" he shrugged and gave a puppy dog look. Dear lord, that was sexy. Hitting him upside the head, Blair laughed and began lean back more comfortably in her seat.

"You know," he said, cocky smile back on his face, "I think we just might become friends."

Rolling her eyes, Blair couldn't keep a straight face as she said, "Don't get your hopes up."


	3. Chapter 3

**Title: Time Will Tell**

**Author: RightSide**

**Disclaimer and Summary: See Chapter 1**

**About Characterization of Blair- Remember that at this point in the show Blair has no one. Then in comes Dean saving the day and rescuing her. I think she might make a small attempt at civility, no matter her prior history. Also, she's being more playful and carefree, which is just a quality I think Dean would bring out in her. I am going to explore it further. Until then, just roll with it please. Thanks…**

**Chapter 3-**

"A party?" Dean's voice was questioning and clearly unhappy. They had sidestepped her parents and their prying. Fortunately her explanation had been enough for their inquisitive minds. She was safe, and after a thorough inspection by a doctor, as healthy as could be expected. Her body was still recovering, but the bandages were no longer required twenty-four seven. Blair was told to let the wounds breathe and that some of the tissue damage would never repair completely. Unlike what she had first thought, there would be scars.

The more she gazed upon her mutilated arms and legs, though, the more she wanted them to be seen. Let them attempt to mock her. Now, more than ever, Blair realized how little this world mattered. Down there, deep in the crevices of the Earth, she had been held captive. The monster had not cared that she was a _Waldorf_ or how many zeroes were in her bank account. It had wanted her blood, plain and simple. A precious commodity every person on the planet possessed.

Then a man with nothing to his name, no fortune or hint of glamour, came to her aid. He cared for her; he slept on the floor beside her after she had offered him a place in her bed. "It's not that I'm not tempted," he had said, eyes sparkling, "But I like you too much for that."

However, her mother insisted on hosting a ball in celebration. Of what, exactly, Blair did not know. Was it because she had returned in one piece? Or was it because she had not run away, as everyone had thought, and bestowed shame on the family? No matter the reason, she still needed a date. Nate and Chuck would come to the gathering out of respect and inability to beat the vicious cycle of parties and meaningless nights involving drinking and pointless conversation.

Staring into Dean's uncertain gaze, Blair pouted her lips.

"You'd better not be expecting me to wear a top hat and coattails," he finally answered, making Blair jump up and wrap her arms around his neck, "And no dancing." Blair lifted an eyebrow.

"Why no dancing?" she asked, arms still on his shoulders. His hands had instinctively gone to her hips, thumbs rubbing circles into the bare skin between where her shirt and pants didn't quite meet. It felt right, somehow. Intimate in a way that she was not used to. Nate's motions with her were always anticipated. Everything seemed played out, as if they lived their lives to a script. With Chuck, it was all about sex.

Dean didn't answer her. He had attempted to for a moment, taking in a deep breath as if he was trying to form words. But by then she had kept up their eye contact for far too long. His motions on her sides stopped as they found themselves trapped by one another. Blair avoided people's stares in general. It always gave her an unnerving, naked feeling that made her shiver. Now, though, she was gazing into those wonderfully honey colored pools without fear. The intensity was striking. At some point after Blair began to analyze the exact shade of Dean's irises she noticed that his face had softened dramatically. The world held its breath for an immeasurable instant, during which both gradually drew the other nearer. Then time sped up, and Blair hardly had time to let out a startled gasp as Dean closed the remaining inches and pressed his lips against hers.

The kiss was not rushed in any way. Dean took his time, drawing out the very simplest movements with ease. His hands crept from her sides up higher so that his fingers splayed against her stomach. Blair's lips curled into a smile which was soon broken as he suddenly pushed his palm into the small of her back, making her sigh as their bodies came into full contact.

Yet he didn't take it any further. There was no pulling of clothing or guttural noises. As they parted, Blair kept her eyes closed tight. His lips hovered over hers for another minute, lightly touching at times, almost as if he was dancing around the idea of stealing another kiss but not daring to press his luck. Finally looking at Dean, she found something she had not expected. There was no lust or cocky smirk. Only a broad, charmingly boyish smile.

"Maybe one dance." he whispered, resting his forehead against hers before placing a chaste kiss on her cheek.

"How am I going to face them?" she took his hands into her own, "Why can't the world just stay like this? Everything with you seems so simple." Dean released one of her hands. She frowned at first, missing the feeling of his fingers intertwined with hers, but then she watched as he lightly stroked the skin next to one of the many slices in her arm.

"So, maybe you don't live your life like a Queen B anymore. Maybe you just stay off the grid. Do what makes you happy."

"That was a bold thing to say." her eyes began to twinkle as she formed a plan.

"Why?"

"Because there is only one thing that makes every girl happy," Dean groaned as Blair excitedly pulled him towards the door, "If you're a good boy, I might stop by the swimsuit section before we leave." At that, he picked up the pace slightly and struggled less, unaware of the fact that as soon as they stepped out of the building together someone snapped a close-up.

Blair's phone sounded unexpectedly from the text message she received. Opening it up, she laughed and showed Dean.

"What's this, Upper East Siders? B out and about with a new Prince Charming? Look out, N _and _C. The war is on for who will have the best arm candy at the upcoming ball, and it can't get much sweeter than B's latest accessory. You know you love me. XOXO. Gossip Girl." Attached was a picture of Blair and Dean hand in hand as they exited her home.

"Congratulations, Dean," Blair said as they took their seats in her limousine, "You've just become a lead in Manhattan's high society."

"You're serious? Gossip Girl?" Blair nodded gravely, "Man, you people need to get lives." Blair was going to take his comment very personal, but began laughing before she had the chance to give him the cold shoulder. He was right, of course. He had been right about everything so far.

Looking around, Dean raised his eyebrows, "I could definitely get used to this. Damn!" Pressing one of the many buttons on his armrest, he managed to get the sunroof open. Glancing down at the stereo controls, Blair smirked. Flipping open the i-Pod, she made sure the speakers would be blasting before she pushed play.

"Hey, hey, Mama, said the way you move, gonna make you sweat, gonna make you groove!" Dean's face lit at the sound of Led Zeppelin. Standing, Blair drug him up with her. He grinned and started playing an invisible drum set. Then he started singing, his cell phone playing the part of the pretend microphone. Finishing the chorus, he turned to Blair and shoved the antenna in her face. Taking the hint, she started belting the song into it, making dramatic, over the top gestures as the song ended. Realizing that her i-Pod was on shuffle, she dived back into the limo to save herself from sure embarrassment. The last thing she wanted was for Brittney Spears to come on.

Dean was quick, though, and grabbed hold of her waist. Dragging her back, he fell onto the floor when she wiggled enough to knock him off balance. Smirking with triumph, she turned back to the seat where her i-Pod sat untouched. As she turned, her high heel caught on Dean's pant leg, and she, too, was sent spiraling to the ground.

"Some people call me the Space Cowboy, yeah. Some call me the gangster of love." the stereo sounded, and Blair breathed a sigh of relief. Dean went into hysterics next to her, holding his stomach. Her entire predicament seemed to amuse him to no end. Straddling him on the ground, she frowned.

"Was that really worth the trouble?" he chuckled. Eyeing him for a moment, she scowled playfully and retreated back to her seat.

--

Nate held onto Jenny's arm tightly as he entered the ball. Stunned into amazement, he had to admit that even for a Waldorf's party it was more elegant than usual. However, there was an extra air about it this night that was lacking during all of the others. Comfort. The room itself was ravishing, the building set to perfection, and yet there was an odd sense of warmth about it.

The blond beside him gasped and pointed, still naïve to the customs of the wealthy. No one showed interest. It did not matter who it was, where it was, or how magnificent it seemed. Unless it was a direct remark to the hostess herself, it was seen as undignified to give praise.

"Would you like something to drink?" he asked his date graciously. She nodded and headed over to a group of girls chatting pleasantly in the corner. Walking toward the punch fountain, he haphazardly noticed that it had already been spiked. Reaching for the cup closest to him, Nate collided with another hand reaching for the same one.

"Sorry, man. I didn't see you there." the stranger said. At first Nate was going to dismiss him completely with a smile and nod, but then he realized that he was the man from the photograph that was sent to his phone hours earlier. Interest peaked, he stretched out his hand, introducing himself.

"Oh! You're that guy!" the man shook his hand and continued, "Dean Winchester. Nice to meet you." Caught unawares by Dean's congenial attitude, Nate fumbled.

"What do you mean 'that guy'? Have we met before?" he asked Dean who had just shoved an amazingly large amount of food into his mouth at once. It seemed he was going to try to talk through the mass, but decided instead to chew and swallow first.

"No, we haven't met. But Blair's been telling me all about life here, you know, with the riches. She explained you guys to me today when we were shopping."

Nate clenched his jaw in an effort to remain calm. What happened between him and Blair was personal; it certainly was not entertainment to offer the first rebound to come her way. Upset about this recent development, he hardly noticed Jenny when she came to take her place on his arm. Remembering his manners, Nate introduced her to Dean and after another show of handshaking Jenny took her drink and fluttered off to join the others.

Nate didn't miss Dean's smirk.

"What?" he asked, taking his time to reevaluate his opponent. Dean wasn't from the Upper East side, of that he was sure. While the rest of the males in the room were in tuxedoes and making serious efforts to appear to be gentleman, it was obvious Dean was not cut from the same mold. He wore slacks and expensive new shoes, and his shirt was freshly pressed, but there were slight details that gave it away. He was not wearing a jacket and his collar was undone; his hair was not gelled into place and stuck out in all directions. Even his body language was nonchalant.

"Nothing, man," Dean set his mouth at a smirk, "I'm just here for Blair. Girl's been through Hell, you know? I'm not going to ruin her first night of fun just because I hate the idea of these things. Balls!" he laughed as if it was the most absurd thing he had ever heard of. "Seriously? Gossip Girl? People spying and taking pictures from the bushes? You guys are in need of help. Go see a doctor, a shrink, take some pills, whatever. But living life this way?" he took a swig from a flask he pulled out from somewhere in his trousers, "It's just plain wrong."

A pair of familiar hands wrapped around Dean's waist, and Nate watched as Blair kissed his cheek and pulled him close. She was standing before him, a goddess, in one of her mother's dresses. It had to have been specially made for tonight. In a smooth, silky, auburn, her gown fell past her knees in strips of fabric that either managed to hide her soon to be scars or accentuated them depending on the angle from which you looked. Her hair was pulled up and draped down her back in a soft bed of curls.

"I see you two have already met!" she said excitedly, standing in front of Dean, his hands at her waist in a very protective hold. Nate remembered doing that from time to time, first out of duty, then habit, and towards the end because he realized how easily he could lose her. Yet he lost her anyway, to this man with no history and no care or sense of where he was.

"He cleans up well, doesn't he?" Blair continued, unaware of the tension, "I tried to get him to wear a tie, but I was lucky he held still long enough to measure his pant size." Nate eyed her again, wondering what on Earth had Blair glowing so intensely. It couldn't all be because of this newcomer, could it?

"So, Dean Winchester, what do you do? You must be twenty? Twenty-one?" Blair froze in place, narrowing her eyes and giving him a look to kill.

"Nate, here," she said, turning back to Dean, "is just worried about me is all. Pay no attention to him. Let's go." And then Nate watched her walk away, the man beside her swaggering, whatever he had just said to the lovely lady making her burst into a fit of giggles.

--

"Is he still watching us?" Blair asked, still laughing at the sight of Dean's perfect waltz.

"No, but someone else is." Dean nodded over his shoulder at Chuck sulking in the shadows. Blair squinted to make sure he was person. Her suspicion was confirmed as he ducked as soon as he realized she was staring back.

"It's Chuck." Blair whispered, knowing Dean would understand her need to hide. Earlier that day she had explained everything down to the smallest detail. There was nothing she kept to herself. If he was to receive odd looks from her former allies, he deserved to know the real reasons why.

"Ah. Well, then," Dean's voice showed his amusement, "let's put the son of a bitch in his place." Once again, Blair didn't have time to retaliate. By the time she realized the full extent of the situation, she was already in the middle of one of the most heated kisses she had ever experienced. Dean's body was in complete contact with hers. There was no stopping the moan that escaped her lips as his teeth scraped her lips. When he released her mouth, he kept his hand on Blair's back to help her keep her balance as she tried to regain her bearings.

"What was…" analyzing him, she scoffed at his wolfish grin, "That will never happen again. You think you're allowed to pull off stunts like that whenever you want? I have appearances to keep, and I do not permit-" He cut her off with his lips.

"Don't do that," he whispered, knowing their close proximity would help his case as her judgment clouded, "Put the Queen B routine away for a while, because I really can't stand it. You're _better _than that."

"Better than what? This is who I am, Dean," she made sure she kept her voice low as they continued to dance in the center of the floor, "This is the world I live in, and just because you don't understand it doesn't mean you can dismiss it like it's trash. This life, it's all I have."

For a moment she thought he was going to do something reckless and stupid. She could see the glint in his eyes, the hint of change that showed something was about to happen. But then a sad smile came over his face as he spun her round.

"Then I'm sorry for you," he stopped, bowed, and kissed her right hand, "I'll keep watch and make sure you're safe. Enjoy your party, Ms. Waldorf."

Blair stared in disbelief as Dean gracefully dodged through crowds of people and exited the room. She was still standing there when the song ended, and didn't even notice Chuck following her as the next dance began.

AN: Reviews are much appreciated. :)


	4. Chapter 4

**Title: Time Will Tell**

**Author: RightSide**

**Disclaimer and Summary: See Chapter 1**

**A/N: First, THANK YOU for your reviews! You guys are amazing! Secondly, this chapter is set hours after the last, just to clear up any confusion in the beginning. Hope you like! XOXO.**

**Chapter 4-**

Out on the terrace, Blair sipped absentmindedly at the glass of champaign in her hand. A miniature wall stood before her acting as a barrier, but how it was meant to protect her from harm, she did not know. It was a deadly fall, that much was true, but why would someone place something so unremarkable as a wall there to deter random moments of stupidity? As if testing her boundaries, she gingerly placed a foot on a large ladder she found leaning against the side of the wall to the far right of the door and hopped onto the ledge.

Carefully lying down on her back, her left foot dangling precariously off the edge, she gazed up at the stars. So beautiful. Her thoughts swirled in a mess of alcohol induced philosophy that had her craving some place where the lights of the city were dimmer. For the first time in her life, Blair regretted being where the others were and wished for nothing more than some isolated place where she could lie and stare and wonder. Or maybe not completely isolated. Dean could be there.

Glaring at the florescent light across the street, she rolled her eyes. If she really wanted to see the stars, she would need to get up higher. Glancing back at the ladder, she smirked. Sitting up and- with a surprising feat of balance- standing on the top of the wall, she stepped back onto the ladder with grace. Swallowing the last of her drink, she placed it on the ledge before continuing her journey upward. There was some sort of slamming sound beneath her, perhaps on ground level, but she couldn't bring herself to care.

The ladder itself was easy to climb, but once on the actual roof she took care to remove her shoes so she could keep steady. Scoffing at the heels, she felt as if they mocked her. They stood for everything she was currently against. Her bond to this world, to the status wearing such expensive, uncomfortable things created. Letting out a small yelp of liberation, she held them over the edge and let them fall. Making her way to a safer area, a random hiccup set her off balance just enough to make her have to catch herself on her hands and knees. Laughing, and feeling more than a little ridiculous, she sighed and rolled over to get a clear view of the vast picture above her. Shrugging off the wrap she had tied about her shoulders, she bundled it up to use as a headrest. Wiggling until she was completely comfortable, she smiled.

And there, on a rooftop, Blair Waldorf lied in a priceless, one-of-a-kind dress. Her eyes were sparkling, her arm lifted up to trace the random shapes she found hidden in the sky. And when Chuck Bass showed up, ready to stop her from doing some imbecilic thing like jumping, he was caught by complete surprise. A pain spread through his body as he studied her, a strangely innocent expression on her face.

When she caught him staring, he thought she would yell and scream. Instead she just turned back to what she was doing before, hand coming out to pat the spot beside her in a friendly gesture. Curious, he took her offer and laid down beside her.

"Chuck." she stated simply in a sort of greeting.

"What are you doing up here?" he asked, trying to analyze the look on her face as she turned towards him.

"Are you happy?" the question came from no where, yet her voice was unbelievably calm. It scared him. A few weeks ago he would think she was toying with him, but lately everyone had noticed that Blair was not who she used to be. After the kidnapping she didn't speak to anyone beside that Dean character, and when she had to make conversation with someone else she kept it simple and impersonal. Not that he cared what she did, or what she went through. It just bothered him that it was such a mystery. The only information anyone could pick up was that she was taken by a knife happy man who was killed by Dean. No descriptions, nothing definite. Just gossip.

"I don't think I've ever been," she thought aloud when he did not answer, "I hate this person that I am, and I always thought that it was the only choice I had for so long. Do you think a person can change, I mean really change? After everything we've done to each other, to people we've never met, do we even deserve to be happy?"

"Where's this coming from? Your new friend?" he spat, hating the idea of how close she had gotten to the man no one knew. How dare he judge her! She was a Waldorf, what did he expect? For her to be humble? Of course she wouldn't be. She would fight. She would want as much control as she could, and she would not regret a single step she took getting there.

"He's a part of it," she admitted, diverting her eyes, "You're a part of it, too. And Nate. And Serena and everyone else."

"How?" his tone softened as he attempted to seem understanding. It was difficult; he wasn't used to acting like he cared.

"What you said to me the last time we talked. When I came to you in the-"

"Blair, you can't think-" she held a finger to his lips.

"It's done. What you said to me then. That I wasn't worth it. That there was nothing special about me," Chuck had to ignore the rising bile in his throat as she continued, "You were right, Chuck. I'm not worth it. Any of it. Someone almost died to save me, and I can't help but think what a waste that would have been."

"Stop it, Blair. Stop talking like this. This isn't you." he could no longer hide his worry. Running a hand through his hair, he waited. Her response never came.

Mentally cursing both himself and her, he became frustrated. What had she come up to the roof for anyway? At first he had thought it was suicide. When he came outside onto the balcony and saw her just as she disappeared onto the roof, he was certain that she had a death wish. She was trashed. Everyone had witnessed her slight breakdown after her knight in shining armor left her on the dance floor. What had he whispered to her? How was it that a man she had known for merely days could drive her to something so uncharacteristic.

A single tear formed in the corner of her eye. Chuck watched as it slid with purpose down the side of her cheek, eventually falling into her hair and out of existence. The trail was still glistening in the eerie light that the moon set bouncing about them, and he couldn't think of a single instance of her crying in the entirety of his time with her.

"What really happened, Blair?" he was about to let his hand trace over one of the scars. But his hand never reached her skin. She shrunk back from him, the fear in her eyes obvious.

"I'm sorry," she apologized, almost as if she had just realized what she'd done, "He looked like you."

Eyes wide, Chuck was stunned into confusion, "I thought you never saw who it was. You were blindfolded or-"

"Honestly, Chuck," she nearly sounded like her old self, "people like us aren't allowed the luxury of telling the truth."

"But the police. I thought you told them you couldn't see."

"I did say that. I couldn't tell them what really happened. They wouldn't understand. And Dean…" she sighed, "They would have blamed him somehow. I couldn't do that. Not after what he did for me."

There was such reverence in her voice. Chuck couldn't help the envy racing through him. Even when she spoke his name she said it gently, as if he was something precious. As if she was some little girl trapped in a dream hoping that while the prince was not yet hers, in time there was no doubt love would eventually come to them.

"So, what really happened?" he didn't want to pry. He knew he had no right. But someone had hurt her. He hadn't wanted to believe it at first when he heard the news. He thought it was a stunt, something utilized to get the attention of the upper east side. Pictures had been posted on Gossip Girl when she returned, bandages everywhere. It could have been a ploy. Gauze covering up unmarked skin.

Tonight everyone had been proved wrong, including him.

"I was asleep when I heard it," she began slowly, "When I finally woke up there was someone by my bed," turning to him, she grimaced, "It was you."

"You mean someone that looked like me." he clarified.

"No. I mean it was you. To the smallest detail. You started asking me questions. How I was. If I could forgive you. It was everything I wanted to hear at the time. It wasn't enough, though; I still wouldn't let you get close. So you stepped up and said you loved me. That was when I hugged you. Him. Whatever it was."

"I don't understand."

"Just pretend you believe me, okay?" she sounded desperate, "I don't know who he was, but he was you until I touched him. Then everything changed. He grabbed me. He was so fast," she paused, hand at her brow, "I couldn't fight him. Then I blacked out, and when I came to I was underground somewhere. He had me chained up. I screamed and I screamed. And then he came back, but I couldn't see him. It was so dark. He tore up most of my clothes and started cutting me. Only one at a time in long slices. Then he would lick up the blood. I can remember it. All of it. His tongue. The knife.

"He stopped midway through a cut and left. I knew he was going to come back. Either that or leave me there to die. But he never did. Dean came and picked the locks. I fainted from the blood loss, and he drove me to a friend of his who was a doctor. He stitched me up, and then Dean took me back to a hotel. This is what Dean does. He tracks people, bad people. Like a vigilante. He's only here because he thinks I might still be in danger." There was a silence that held a mixture of awkwardness, tension, and pity. He hated all of them. He hated what she had just told him. Of all the scenarios he had imagined, that was never one of them. To think of Blair in the dark screaming as a man slit her open piece by piece… he shivered involuntarily.

"I'm sorr-"

"Don't," she said harshly, "I don't want your sympathy." Instead of acting upset or even annoyed, Chuck merely leaned back on his hands and sighed. After countless moments staring into nothingness, Blair scooted closer to him, hand moving to cover his. He made sure she couldn't see him smile.

"The only time I can remember being happy," he said, making sure his attention was focused solely on some unrecognizable cluster of stars, "is with you. Only with you."

Untangling her fingers from his, she shook her head, "I can't believe that."

"It's true. I've never been one for lying to girls to make them feel better. You know that better than anyone." He didn't try to reclaim her hand. Her reaction left him feeling unbelievably cold. It wasn't '_I don't_ believe that'. She had said _can't_. Almost like she would not allow herself to feel for him.

"I need to leave. I have to go back." _to Dean_. He knew she had omitted the words, but they still hung in the air as if actually given breath. Standing first, he helped her up and held the ladder as she climbed down. Once he, himself, reached the terrace he found that she had already gone. Running back to the main room, he watched as she slipped out the front door.

Laughing at himself, he couldn't believe what a fool he was. Had he thought her opening up was some sort of breakthrough for their relationship? That she would come home with him in his limo and repeat their first night together? It was a ridiculous notion. As if she would ever like him that way again. She had a savior, someone who had proven his worth. How could he compete?

"Hey there," a random red head stood in front of him, dress low cut enough to leave very little to the imagination, "The party's getting dull. Want to get out of here?" Chuck blinked several times, awed at his hesitance. That couldn't be good. Out of sheer reckless defiance he forced himself to speak.

"Meet me outside in ten."

**A/N: No worries, the next chapter will be VERY Dean filled. It killed me not to have him show up on the roof and sweep Blair off her feet. Please review!**


	5. Chapter 5

**Title: Time Will Tell**

**Author: RightSide**

**Disclaimer and Summary: See Chapter 1**

**A/N: Well, I'm admitting that Dean might seem a little OOC, but that's because I'm writing him the way I would picture him as a twenty year old as opposed to the twenty-six year old in Supernatural. Just a heads up in case someone is irked by the characterization. Other than that, there's no serious business to attend to. Thank you SOO much for the reviews. Enjoy the new chap.**

* * *

**Chapter 5-**

"There are at least two more hiding out somewhere in the sewer system. I was able to track the one to an old feeding ground of theirs, but the others were long gone by the time I got there," Dean reported as he casually slung a loaded shotgun over his shoulder. Staring up at him from where she sat on the bed, Blair was convinced she had never seen any man look more attractive than he did at that moment. He had changed clothing since his adventure, but he hadn't had time to shower yet. Beneath the loose black shirt there were still some visible patches of grime.

"Are you listening to me?" she jumped. Had he been speaking? Still staring at a bit of dirt on his neck, she stood and slowly sauntered towards him. Narrowing his eyes, Dean knew what she was going to do. She had given him ample time to both realize the situation and assess it. The moment to push her away approached and passed without occurrence.

Blair stood on her tip toes and kissed his jaw line. Dean stayed perfectly still, body rigid as she continued to press her lips further down the curve of his neck. Right hand on his arm, she began to move it down until it rested on the hem of his shirt. Pulling away, she never broke eye contact as she slid the fabric higher and higher on his chest. Accommodating her, he rose his arms to make the process easier before placing them back at his sides.

Soaking in the image of him, she gazed hungrily at every inch of skin. As she trailed her fingers from his collar bone to the slope of his jeans and back she noticed that he had closed his eyes. She wanted to memorize him. If not because he was quite possibly the most beautiful thing she had ever laid eyes on, than because she knew how close she was to losing him. Today he had been gone all day hunting. Tomorrow he will leave again. And the next day, too, until he was sure she was safe. When he finally left after that, she knew he wouldn't be coming back.

Caressing his scars and faded bruises, Blair found herself gingerly kissing each one. Every time she touched him his breathing hitched, his fingers clenching just a little tighter. As she leaned down to what appeared to be an old knife wound, she felt Dean suddenly step back.

"What's wrong?" she asked timidly, praying he wasn't rejecting her.

"I can't, Blair." he was hesitant as he said the words, as if in disbelief that he would give them breath in the first place.

"Why not?"

"You barely know me. If we start this now, I don't know if I'll be able to stop."

"But I don't want you to stop."

He shook his head roughly and paced, "You say that now, but I won't let you do something you're going to end up regretting-"

"Stop it!" she screamed, and Dean paused his motions to stare blankly at her, "Stop trying to save me, Dean. Just stop. Please." Blair took in a deep breath before finally rebuilding enough courage to kiss him fully on the lips. Once again he was unmoving, standing stock-still as her tongue played over his. But she wouldn't let him stay frozen. Pushing him backward until his knees hit the back of her computer chair, she waited for a moment before straddling him.

As predicted, her assault on his lips didn't remain unanswered for long. Giving in, Dean's fingers began to tangle in her hair, arm curling around her back to bring her as close to him as humanly possible. Blair gasped as the kisses progressed from lukewarm to a form of desperation she had never known. He was acting as if he needed her, all of her at once. Before she knew it, her own shirt had joined his on the ground and in a flash his fingers managed to unhook her bra. Wrapping her legs about him as he stood and carried her to the bed, she noticed a change. Now instead of enveloping her he drew his nose along the smooth line of her neck. Placing feather light kisses here and there, he spun lazy circles against her stomach with his hands.

"No one's ever done that to me before." he said, moving to lie beside her for a moment, his finger's movement on her neck making it difficult for her to concentrate.

Trying to laugh away the sudden seriousness, she flippantly answered with an, "I'm sure I'm not the only girl to come onto you." His forehead came to rest against hers, lips hovering before finally descending upon her in a deliberately unhurried, passionate kiss that lasted for what seemed like an eternity. With no pressure, Blair allowed herself to bask in the intensity of it all. To think she had believed herself to be so in love with Nate, so mesmerized by the touch of his lips and the softness of his skin. It was only because she had never experienced the perfect shape that Dean had to offer, the wonderful shudder that raced through her spine as his calloused hands pressed against her body.

A whining sigh escaped her as he let go. Lifting her chin, he seemed to be searching for something Blair wasn't sure she had the capacity to possess. Sifting through the fog that was her conscious mind, she felt like she was grasping at straws. Everything she wanted to say was so inappropriate. But even though she didn't want to do anything to lose the moment, she knew it had to be done.

"If we do this, I don't think I'll be able to let you go." _If we do this there won't be any going back. If we do this and you leave me, I won't survive it._ She had sex with Chuck for ridiculous reasons; because she was angry or feeling adventurous to name a few. With Nate it was a mixture of revenge and some shimmer of hope that she could force their relationship into what it could have been.

And now it was because she wanted nothing more than him. To be complete, to devote herself entirely to him. The idea made her both elated _and _incredibly frightened. If she offered him the world, her world, only to be thrown away afterward she had no clue how she would react. Blair was certain there was nothing that could cure that pain, which is why she needed to be certain. Waiting for his response, watching as a lifetime of choices and decisions flashed behind his crystal green eyes, Blair remained silent.

"That's not a choice I could ever make."

Frowning, Blair replied, "But I could." Dean's entire body tensed, surprise flooding his features.

"You would do that for someone you've only known for a couple of weeks?" he asked disbelievingly.

"No," she admitted, and noticed his eyes fall, "Not for someone. But for you? Yes, I would do it for you."

"But why?"

"Because you're sexy," she grinned, then whispered softly, "Because you amaze me." At some point their fingers had laced, and she brought his hand to her lips to place a chaste kiss there. He stared at her the entire time, his expression ranging from astonishment to apprehension.

Despite the situation and the gravity of the conversation, Blair found herself yawning.

"How about this," Dean began, sitting up a little more, "We don't have to decide now. It's been a long day. Let's just go to sleep. The big bad monsters won't be up and around to track until later on in the day, so we'll spend the morning together, just us." Blair smiled although her better judgment told her he was just beating around the bush. And her better judgment never lost the proverbial battle.

"So you're saying you're not sure if you want me." she clarified.

"No!" he practically growled in frustration, "I'm saying you'd be giving up a lot for someone you haven't spent that much time with."

"Who says I'd be giving up anything?" she smirked, "Say I go with you. You kill demons, I stay at the hotel helping with research. We fight, and I end up wanting to go home. I'll have a job at my mother's company waiting with a starting salary that would have me living very comfortably." She continued on with the hypothetical until she was practically laughing. She had to, because while the thought itself was very realistic she needed Dean to know it was only said to poke fun.

"So you would really want to come with me?"

"Yes, I really would," smiling, she reached down to pick her shirt up off the ground, "But sleep does sound good. As long as you stay here with me, that is."

"Your mother-"

"Is away in London for a few days interviewing male models for the European photo shoot. There's nothing to worry about," Dean gave her a very insinuating look, "I'll behave, I promise. These hands won't go anywhere you don't want them to. Scouts honor."

Laughing a little at the sight of Blair saluting him with lipstick smeared and hair looking as if she had just survived a major hurricane, Dean ventured into the bathroom to leave her some privacy to change while he, too, got ready for bed. Emerging after a few minutes in an AC/DC tee and blue plaid boxers, he smiled appreciatively at Blair's figure. The lacy white tank and bright yellow shorts contrasted nicely with her slightly tanned skin.

After exchanging random pleasantries the two motioned towards the bed. Blair rolled her eyes at the awkward tension hanging in the air. Why had things been so easy when the close were off? Obviously Dean was feeling it too, he was practically forcing himself to keep a half hearted grin. Refusing to let this get the better of them, Blair edged her way over to him and rested her head on his chest, loving the way heat radiated around her as she listened to his heartbeat. Relaxing, he put his arm around her and began softly stroking her chestnut locks. Closing her eyes, Blair could feel the transition coming over her as she drifted off into sleep. But as she stood on the brink of oblivion, she heard Dean begin to speak.

"Earlier, when I said a girl had never done that before, I didn't mean what you thought I meant." Confused, Blair yawned before attempting to comprehend what he had said.

"Then what did you mean?"

"I've never been," he paused, unable to find the words, "I've been with plenty of girls, but none of them ever… none of them ever looked at me the way you did. No one has ever touched me like that, or…" he trailed off. Blair understood. He wasn't used to showing his emotions, and there he was laying it all on the table. Smiling, she raised herself so that she was upright, fixing the pillows so her back was comfortable. Watching her, Dean threw her a questioning glance. Motioning for him to move beside her, he smirked a little and laid down.

And there they slept, Dean lying in Blair's arms, her hold on him somehow both protective and tender at the same time.

* * *

_While the Queen is away, the children will play. S, N, and C have been doing some old fashioned bonding. Or is that plotting? Better step up, B, or you might have a full on mutiny on your hands. You know you love me. XOXO. Gossip Girl._

* * *

"I'm just saying, what if this wasn't all by accident?"

"Explain." Serena commanded, rubbing her temples tiredly. Chuck rolled his eyes and gave Nate an exasperated look.

"He's saying that this guy, Dean, randomly came out of no where. Who's to say he wasn't a part of the kidnapping in the first place? The first guy grabs her, tortures her, and the next guy acts like the knight in shining armor. The girl takes him back to her place, they get friendly, and he gets his pay off. The girl's too blinded by admiration to realize she's just been manipulated, and he's gone before she has the chance to track him down."

"It's been weeks, though. If that were the case, he would have left by now."

"Not if Blair hasn't been putting out," Nate interjected, "He might be sticking around a while longer just to get in her pants."

"I say we get him gone. For good." Chuck said seriously.

"Agreed."

"Wait!" Serena just couldn't make any sense of it, "What if this guy really is the genuine article? What if-"

"What if what? Honestly, what potential do they have, Serena? He's a twenty something year old guy with no job and no future. I mean, you can believe that he's the dashing hero all you want, but in the end it's not going to work out. He's going to leave, and she's going to be left in pieces. Is that really what you want for her?"

"And what do you want for her? Huh, Chuck?" Serena accused, "Why do you care so much all of the sudden? You didn't seem to mind when you broke her heart. Or you, Nate. You said you wanted nothing to do with her. Please tell me this isn't just some trick to get her away from this guy so that you two can have the satisfaction of knowing that she's alone."

"If you really believed that," Chuck leaned forward, the clinking noise of the ice in his glass piercing through her, "then you never would have called us in the first place. You were the first to voice your concern. Now are you with us or not?"

Blair was her best friend, the one who pulled her out of the mess she had gotten herself into with Georgiana. If it wasn't for her, Serena would still be boozing up with some low life scum, losing all of her dignity in the process. She owed it to her to stop this. Although she hated to agree with Chuck on any matter, she had to admit he was making too much sense to ignore. Even Nate was with him, a feat in itself.

"What do you propose we do?" she asked, finally surrendering.

"What we always do. Dig for as much as we can as fast as we can. Find a weakness. Everyone has a price." Chuck looked to his friend for any other ideas.

"Serena, why don't you go to Blair's," at her confused expression, Nate continued, "Find out what exactly their relationship is. Get some more information for us to work with. Maybe even see if you can talk some sense into her. Show her reason." Nodding, Serena gathered her things and left. Just as she entered the elevator, Nate caught her arm.

"You didn't betray her by calling us. You were being a good friend. What you're doing, it isn't wrong."

"Yes it is. But it's necessary." Staring at the ground, she didn't bother looking him in the eye as the doors closed.

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**A/N: Reviews anyone? You know you want to… :)**


	6. Chapter 6

**Title: Time Will Tell**

**Author: RightSide**

**Disclaimer and Summary: See Chapter 1**

**A/N: So, this chapter might seem a touch confusing, but bear with me please. Sorry if there are some inconsistencies with Dean's age compared with Sam's if you are a Supernatural fan. And if Chuck seems a little off, I apologize. But I love his character, so this is what he's doing in my fanfic. If it bugs you, feel free to rant.**

**Chapter 6-**

"But come on, the entire series was amazing. I mean 'This is my boom stick!' is classic." Dean argued, unable to believe what he was hearing from this guy. Some people just had no taste.

"The writing was pretty bad ass, I'll admit, but couldn't they have tried a little harder? In Evil Dead the characters are a bunch of college students, and then in Evil Dead 2 they changed the whole plot around. It isn't even a sequel. It's just a redo of the first one."

"Dude, it's awesome, so who cares? Are you telling me you would have rather had it be another Night of the Living Dead? The first couple are great, but when they stretch it out into a fourth and fifth and sixth it just gets ridiculous. Army of Darkness was just as good as Evil Dead, maybe even better."

"Yeah, but why couldn't they have just called it Evil Dead 3? They didn't give Evil Dead 2 a different name." Dan countered.

"Oh, come on! The guy fell into a wormhole and was transported into the dark ages. I think the movie deserves it's own title."

Grabbing another Coke from the fridge, Dean asked his new friend if he wanted any. Weighing the can in his hand, Dan replied that he still had some left. Glancing at the stairs on his way back to the living room, Dean shook his head. The girls had been up there for almost two hours. Serena and Dan had shown up and after a battle of wills the blond managed to drag Blair upstairs to have a private talk. It didn't take a brain surgeon to figure out what the little chat was going to be about. Serena had been glaring at Dean from the moment she walked in the door.

"So, I have to ask, you seem like a cool guy," Dean began as he sat on the couch opposite of Dan, "And Serena's very… pretty, but I dunno. Don't you think she seems kinda… you know… high maintenance?" Dean had no idea how such a down to Earth guy like Dan could be with such a prissy girl like Serena. She was hot, no question. But when you looked at her, really looked, there wasn't much more. That plus the details Blair gave about her extracurricular activities involving the ex boyfriend made his opinion lean more than a little towards the bad side. She had hurt Blair several times. First by taking away the guy she loved and then abandoning her. Even with the psycho chick, Georgia, running around there was no excuse. Someone being that easily reduced to crazy benders had problems.

"No one gets me and Serena. But I knew, the first time I laid eyes on her I knew. I'm not saying she doesn't have her faults. Her choice in friends for one. Not to make you mad or anything, but Blair drives me insane. She's so… well, I won't even say it. Then there's Chuck and the rest of them. I don't get how she can even pretend that they're decent people." Dean knew he should be upset, but he remembered all too well the thoughts he had of Blair the first time she decided to become the worst version of herself in front of him.

And as for the rest of the group? They were all scheming trust fund babies with nothing better to do than destroy each other for sport. Dan was right. Not a decent human being among them. Besides Blair. Maybe Serena, too. If Dan liked her and Blair still tolerated her, then there had to be some good quality buried down deep.

"You've got that right. I don't know how you put up with it."

"I've been asking myself that, too. But Serena likes it, it's how she grew up. Blair, though?" he gave Dean a wide eyed look and whistled, "That's a different story."

"She can be hard to deal with, I'm not gonna lie. We fight. A lot. But it's not her. It's this place, these people," he rested his elbows on his knees, "And I'm leaving in a few days, a week tops."

"You saved her life, Dean. It's up to her to take care of the rest."

"I know. I just wish…" he trailed off as he noticed that the dynamic duo had finally come out from the room. Watching as they still argued in hushed tones at the top of the staircase, Dean and Dan stood and exchanged looks.

"It's nothing personal," Dan said apologetically as he gave Dean a supportive pat on the shoulder, "They don't like that you're changing things. It means that they don't have as much control as they thought."

"Changing what?"

"What do you mean what?" Dan laughed only to receive two sharp glares from above, "When I walked in here I was expecting the Ice Queen in all her glory prepared to hand out a snide comment. Low and behold she's in the middle of a tickle fight wearing no make-up, hair not done, in a pair of loose jeans and a guy's heavy metal shirt. You've taken the Blair Waldorf and made her… normal. Serena's just afraid you're gonna hurt her. And to the rest of the Upper East Side? You're, well, threatening. I like you. And as a friend I have to warn you that these people may look like a bunch of pushovers, but they've got ways. They'll take away everything if you're not careful."

"Then it's a good thing that I don't have anything." Dean joked.

"You have her," Dan glanced up at Blair as she descended the staircase, "That's more than enough." Serena rushed towards them, face tear struck. Taking her arm in his to console her, Dan turned to give Dean a sad smile before leaving.

* * *

"I cannot believe her!" Serena screeched, throwing her purse down on Dan's bed. Growling, she plopped down and ran a hand through her hair. Grabbing her phone and harshly shoving her fingers into the buttons, she began to text rapidly. With every response she seemed to be becoming more upset, throat rumbling and nails digging into the straps of her coach bag.

Dan observed the entire scene with an eager curiosity. He had never fully understood the plotting process, or the reasoning behind it. When he had turned to Blair for help with the Georgiana crisis, he had been too desperate to care what he was resorting to. Is that what Serena was feeling now? Or had she been doing this type of thing for so long that it no longer took such a strong emotion to make her plan the destruction of another human being?

"You should have heard her, Dan," she began, closing her phone with an air of finality, "I mean, she wasn't even being mean. She just didn't _care_. I tried to tell her, you know. I tried to explain how much she'd changed, and how she was starting to lose her real friends. You know what she said to that?" Dan waited for her to continue, thinking it was a hypothetical, but soon realized she was awaiting his answer.

"I don't know. What did she say?"

"She said, 'What real friends?' Can you believe that? And she started bringing up our entire history. I mean, things I thought we were past by now. But obviously not. So, I thought to myself, maybe if I'm just really direct she'll finally get it. So I told her. I told her that he was going to leave her and that when he did she'd be lucky if she had anyone left. And do you know what she did then?" she didn't bother waiting for his response, "She said she didn't plan on being left." Serena spat the words as if they were acid on her tongue.

"It'll be fine, I promise," Dan whispered as he tried to comfort her, "Dean said he was leaving in a few days. He won't be around for much longer."

"You talked to him?" she pulled back, seeming stunned. Blinking back tears, she began to analyze him.

"You were up there for a long time. What was I supposed to do?"

"Well," her eyes brightened; Dan could see her mind turning, "What did you talk about?"

"A lot of things. Why?" his voice dropped low, face twisting into a mask of disgust. Was she honestly going to do this?

"Chuck and Nate can't come up with anything on him. As far as we know he's a regular John Doe from Kansas with a smart brother, Marine Corp dad, and mom who died when he was little. Maybe if we had someone who he could trust. Someone he could relate to…" she trailed off, the look of hope on her face disguising her true intentions.

Dan smiled sadly he bent his head down low to give her a full kiss on the lips. Slightly stunned, Serena responded gradually, wrapping a hand around his neck to pull him closer. Balancing his weight on his elbows, he lowered himself over her, lips following the trail his fingers made as they deftly removed any annoying pieces of fabric that got in the way. Groaning as she shifted beneath him to make their position even more compromising, Dan quickly released her and took a step back.

"I like him. I'll be friends with the guy while he's here, but I won't help you mess with his head. As far as I can see, he's done more good than anything." Watching as Serena readjusted herself, he awaited her reply.

"Fine. But if he's such a great guy, you won't mind telling me what the two of you talk about."

Dan grunted.

"Fine," he crawled back over her, burying his head in the crook of her neck, "Could you be more of a pain?"

* * *

Chuck stood nervously clutching the end of his trademark scarf. Scanning the entrance again for any sign of his Blair, he clicked his tongue and checked his phone. No new messages. Of course not. They had been searching for days only to end up with… nothing. This Dean was a ghost. A modern day magician with no paper trail, no job. He existed for seventeen years in reclusive holes of random home schooling and not even as much as one trip to the doctor for a cold after age six. It was unnatural, and it made Chuck's life so much more difficult than it needed to be. So he came, without permission from Serena or Nate he stood on the Queen's doorstep lurking, calculating. He could just imagine the headlines on gossip girl.

Seen: Chuck Bass himself sneaking around Queen B's. What's the matter, Chuck? Afraid you might lose what you already threw away?

A flash of perfect brown tresses caught his eye, and Chuck snapped out of his reverie. This wasn't the Blair Nate allowed to cling to him, or the one who would stand in front of the mirror holding her stomach as she trembled before her warped vision of her own starved frame. This was a different creature altogether. She must have gained a few pounds, her arms no longer angular sticks of jutting bones. Her eyes were soft, skin clean, clothing plain, yet passable in terms of society's standards. He nearly gagged at his next train of thought.

She was glowing.

Hesitating with the help of the conscious he was so quickly beginning to tire of, Chuck stood stock still for a few beats before heading towards the double doors. Every instinct he had told him to turn and run. Hell with the girl, let her learn from experience…

The elevator doors opened, and he calmly stepped inside, nodding coolly to the doorman. Attempting to steady his breathing, he began rocking on his heels. Back and forth, back and forth. _Blair needs this. He'll leave her. And when he goes she'll be more broken than before._

The apartment was empty. Checking and double checking, he eventually gave up and poured himself a glass of scotch. Blair was off to Serena's to make peace for the havoc that had occurred the day before. Using Dan as a spy? He chuckled at the mere thought of it.

He had two or three hours before the goddess came home, leaving Chuck with the option of stretching out across the leather sofa to wait. Always waiting. Only this time it wasn't for Blair. It was for Dean. Because Chuck had found the weak spot, buried down deep. And he was willing to exploit it, whatever the cost.

* * *

Blair glanced around the apartment and sighed. If Dean was back music would be blasting and she would have already caught sight of the abnormally adorable grin she had grown to know and love. Fingering the material of the jacket Dean must have haphazardly tossed on the couch earlier, Blair frowned. Hadn't he been wearing it that morning? And if he was already back, where was he?

Slowly climbing the stairs and unconsciously holding her breath, she crept her way to the door to her room. Instantly she recognized the sound of voices, but whose?

"You couldn't. Not even a rich boy like you could afford-"

Dean.

"You would be surprised what a 'rich boy' like me can do." Chuck said. She could imagine him sitting there, lips turned into something that resembled both a grin and a snarl as he watched the wheels spin in Dean's head, knowing that he was already one step closer to accomplishing whatever demented goal he set his sights on. Dean wasn't prepared to handle this. Not yet. He had no practice dealing with the maniacal manipulations of the Upper East Side.

Her heart plummeted. Would he allow himself to be bought? Her knight? She knew she was ridiculously enamored by the sight of him. She knew her affections were horribly childish, but Blair couldn't bring herself to care. In the course of a couple of weeks all of her faith in humanity had come to rest in his hands.

"You expect me to believe that as soon as I'm gone you'll keep your word?" Dean's tone was menacingly contemplative.

"Yes. He's already in. All that stands in the way is paperwork. I have the connections. If Sammy gets a letter saying tough shit, you could always come back and do whatever it is you're about to threaten to do to me."

"You don't understand. I'd never-"

"You'll agree because it's Sam. Your little brother. And something tells me that you'd do just about anything to keep him safe. To let him have a normal life. With my help, you can give him that. Or maybe I overestimated you. Maybe you really are that selfish…"

Damn him, Blair thought. Damn everyone who ever told her life was grand and easy and that good people end up happy and bad people are tossed aside. Hadn't she given enough to earn a chance, just one chance, to be loved? To be happy? Hell, she'd settle for decent. Anything that meant she wouldn't have to be guarded all of the time with only Audrey Hepburn movies to keep her company.

She heard a whisper, a disgusted, self pitying kind of whisper come from Dean. But Blair couldn't listen. Going back to the lobby, she paced and cursed and when she finally saw the elevator open again to reveal a satisfied Chuck strutting out she was in front of him before she realized what she was doing. The slap echoed and every head turned to witness the episode they were so sure was about to occur. Seconds lapsed upon minutes as she stared at him, tears streaming down her face, breath coming out in weak sobs.

He spoke, at first in a stutter and then softly, slowly.

"I had to."

Her head dropped in defeat, in agony, and she walked away.

Chuck watched as her form passed through the doors and beyond the line of cars piled up in the street. Purposefully, as if she knew where she was headed. He knew better than to follow. Somewhere between the look of complete loss on Blair's face and the point when her dejected body vanished in the mass of humanity that was New York, Chuck came to the conclusion that he had made the right decision.

As he glanced back at the building through the tinted glass of the limousine, his nonchalant mask gave way to an exhausted, crestfallen smile.

_"So, do we have a deal?"_

_Dean nodded, "Yeah, we have a deal."_

_"Then we're done here. Tell your brother congratulations on the full ride to Stanford." Chuck stood to leave._

_"You gonna tell her goodbye?"_

_"No," he paused, thinking it over, "If I did, she'd know."_

_"I'll take good care of her."_

_"I know you will," sighing, he managed a grin, "You make her happy. And if any of us deserve happiness, it's her."_

**A/N: Next chapter we will see the response from the rest of the Upper East Side. Will Blair go with Dean? Will she realize how much Chuck loves her? Will she die in some horrible Supernatural accident that makes all of you hate me?**

**Reviews are lovely. Please send some my way.**


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